7. Hugh Hefner and Holly Madison

By Rebecca Winters KeeganMonday, Nov. 03, 2008

If romance can't last between a 28-year-old model and an 82-year-old man who wears a
bathrobe to the office, why should the rest of us even bother trying? Of Hef's three young, blonde girlfriends who co-starred on the E! reality show Girls Next Door, Madison was the most devoted to the Playboy founder. But all was not well in the mansion. Earlier this year, Madison unsuccessfully attempted to get pregnant with Hef. By October she was
telling a TMZ cameraman the 7-year relationship was over. Everyone moved on quickly. Hef, whose other girlfriends, Kendra Wilkinson, 23, and Bridget Marquardt, 35, had also turned their attentions elsewhere, picked up 19-year-old twins with a rap sheet. And Madison started dating magician Criss Angel. Awkwardly, perhaps, the E! show will go on for a sixth season.